Synthesis and lipase catalysed stereoselective acylation of some 3-methylalkan-2-ols, identified as sex pheromone precursors in females of pine sawfly species

Journal of the Chemical Society. Perkin Transactions 1

Volumn 2, Issue 15, 2002, Pages 1810-1817

  HedenstrÖm, Erik ^a   Edlund, Helen ^a   Lund, Susan ^a   Abersten, Malin ^a   Persson, David ^a  

^a MID SWEDEN UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL MATERIALS; CATALYSIS; MOLECULAR STRUCTURE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

DIPRION NIPPONICA; DIPRION PINI; GILPINIA FRUTETORUM; GILPINIA PALLIDA; LIPASE; MACRODIPRION NEMORALIS; METHYLALKANOLS; MICRODIPRIOIN PALLIPES; SEX PHEROMONE PRECURSORS; STEREOSELECTIVITY;

ORGANIC COMPOUNDS;

EID: 0035995717     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b201395a     Document Type: Article

References (40)

1. D.R. Smith, in Systematics, Life history, and distribution of sawflies, Sawfly Life History Adaptations to Woody Plants, eds. M. R. Wagner and K. F. Raffa, Academic Press, San Diego, 1993, pp. 3 –32.
2. O. Anderbrant, Sawflies and Seed Wasps in Pheromones of Non-Lepidoperan Insects Associated with Agricultural Plants, eds. J. Hardie and A. K. Minks, CABI Publishing, Wallingford, 1999, pp. 199 –226.
3. O. Anderbrant, in Pheromone biology of sawflies, Sawfly Life History Adaptations to Woody Plants, eds. M. R. Wagner and K. F. Raffa, Academic Press, San Diego, 1993, pp. 119 –154.
4. F. Östrand, A.-B. Wassgren, O. Anderbrant, G. Bergström, E. Hedenström, H.-E. Högberg, B.-V. Nguyen, M. Larsson Chemoecology.
5. A.-B. Wassgren, G. Bergström, A. Sierpinski, O. Anderbrant, H.-E. Högberg, E. Hedenström Naturwissenschaften 2000, 87, 24-29.
6. G. Bergström, A.-B. Wassgren, O. Anderbrant, S.A. Ochieng, F. Östrand, B.S. Hansson, E. Hedenström, H.-E. Högberg Naturwissenschaften 1998, 85, 244-248.
7. A. Tai, Y. Higashiura, M. Kakizaki, T. Naito, K. Tanaka, M. Fujita, T. Sugimura, H. Hara, N. Hayashi Biosci. Biotechnol. Biochem. 1998, 62, 607-608.
8. G. Bergström, A.-B. Wassgren, O. Anderbrant, J. Fägerhag, H. Edlund, E. Hedenström, H.-E. Högberg, C. Geri, M.A. Auger, M. Varama, B.S. Hansson, J. Löfqvist Experientia 1995, 51, 370-380.
9. A. Hertz, W. Heitland, O. Anderbrant, H. Edlund, E. Hedenström Agricultural and Forest Entomology 2000, 2, 123-129.
10. P. Lyytikäinen-Saarenmaa, O. Anderbrant, J. Löfqvist, H. Hedenström, H.-E. Högberg For. Ecol. Manage. 1999, 124, 113-121.
11. M. Larsson, B.-V. Nguyen, E. Hedenström, H.-E. Högberg Eur. J. Org. Chem. 2001, 353-363.
12. S. Karlsson, E. Hedenström Acta Chem. Scand. 1999, 53, 620-630.
13. E. Hedenström, H. Edlund, A.-B. Wassgren, G. Bergström, O. Anderbrant, A. Sierpinski, F. Östrand, M.-A. Auger-Rozenberg, A. Herz, W. Heitland, M. Varama Manuscript in preparation.
14. E. Hedenström, H. Edlund, A.-B. Wassgren, G. Bergström, O. Anderbrant, A. Sierpinski, F. Östrand, M.-A. Auger-Rozenberg, A. Herz, W. Heitland, M. Varama Manuscript in preparation.
15. E. Hedenström, H.-E. Högberg Tetrahedron 1994, 50, 5225-5232.
16. E. Hedenström, F. Andersson J. Chem. Ecol. 2002, 28, 1249-1266.
17. P. Karrer, F. Benz, R. Morf, H. Raudnitz, M. Stoll, T. Takahashi Helv. Chim. Acta 1932, 1399-1419.
18. M. Kamezawa, H. Tachibana, T. Ohtani, Y. Naoshima J. Chem. Ecol. 1994, 20, 1057-1061.
19. G. Bergström, A.-B. Wassgren, H.-E. Högberg, E. Hedenström, A. Hefetz, D. Simon, T. Ohlsson, J. Löfqvist J. Chem. Ecol. 1992, 18, 1177-1188.
20. Y. Nakamura, K. Mori Eur. J. Org. Chem. 1999, 2175-2182.
21. Y. Ohtsuka, O. Katoh, T. Sugai, H. Ohta Bull. Chem. Soc. Jpn. 1997, 70, 483-491.
22. B. Morgan, B.R. Stockwell, D.R. Dodds, D.R. Andrews, A.R. Sudhakar, C.M. Nielsen, I. Mergelsberg, A. Zumbach J. Am. Oil Chem. Soc. 1997, 74, 1361-1370.
23. M. Lundh, O. Smitt, E. Hedenström Tetrahedron: Asymmetry 1996, 7, 3277-3284.
24. P. Berglund, C. Vörde, H.-E. Högberg Biocatalysis 1994, 9, 123-130.
25. C.-S. Chen, Y. Fujimoto, G. Girdaukas, C.J. Sih J. Am. Chem. Soc. 1982, 104, 7294-7299.
26. P.J. Kocienski, C.J. Love, R.J. Whitby, G. Costello, D.A. Roberts Tetrahedron 1989, 45, 3839-3848.
27. A. Marfat, P.R. McGuirk, P. Helquist J. Org. Chem. 1979, 44, 3888-3901.
28. P.R. McGuirk Tetrahedron Lett. 1978, 2465-2468.
29. D. Raederstorff, A.Y.L. Shu, J.E. Thompson, C. Djerassi J. Org. Chem. 1987, 52, 2337-2346.
30. S. Genard, H. Patin Bull. Soc. Chim. Fr. 1991, 3, 397-406.
31. G. Weitzel, J. Wojahn Hoppe-Seyler’s Z. Physiol. Chem. 1951, 287, 65-89.
32. M.M. Martin, J.G. MacConnell Tetrahedron 1970, 26, 307-319.
33. B.G. Kovalev, F.A. Nasser, A.M. Sorochinskaya Zh. Org. Khim. 1993, 29, 678-681.
34. J. Cason J. Org. Chem. 1950, 15, 139-143.
35. J.A. Marshall, B.S. DeHoff Tetrahedron 1987, 43, 4849-4860.
36. C.W. Kamienski, J.A. Schwindeman, B.T. Dover, R.C. Morrison, Organolithium process, FMC Corporation. US Patent 5,523,447, 1996, 1 –12.
37. E. Hedenström, H.-E. Högberg, A.-B. Wassgren, G. Bergström, J. Löfqvist, B. Hansson, O. Anderbrant Tetrahedron 1992, 48, 3139-3146.
38. G. Magnusson Tetrahedron 1978, 34, 1385-1388.
39. E.I. Negishi, D.R. Swanson, C.J. Rousset J. Org. Chem. 1990, 55, 5406-5409.
40. S. Byström, H.-E. Högberg, T. Norin Tetrahedron 1981, 37, 2249-2254.